US5055603A - Method for the preparation of dialkyl-tin-dichlorides - Google Patents
Method for the preparation of dialkyl-tin-dichlorides Download PDFInfo
- Publication number
- US5055603A US5055603A US07/648,574 US64857491A US5055603A US 5055603 A US5055603 A US 5055603A US 64857491 A US64857491 A US 64857491A US 5055603 A US5055603 A US 5055603A
- Authority
- US
- United States
- Prior art keywords
- tin
- aluminum
- tetrahydrofuran
- triacetate
- dichloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 38
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 19
- WCOATMADISNSBV-UHFFFAOYSA-K diacetyloxyalumanyl acetate Chemical compound [Al+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WCOATMADISNSBV-UHFFFAOYSA-K 0.000 claims abstract description 16
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 10
- 238000004821 distillation Methods 0.000 claims abstract description 10
- 238000001914 filtration Methods 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- WQENOBKKDOBQIX-UHFFFAOYSA-J dichlorotin(2+);diacetate Chemical compound [Cl-].[Cl-].[Sn+4].CC([O-])=O.CC([O-])=O WQENOBKKDOBQIX-UHFFFAOYSA-J 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 abstract description 5
- 230000001376 precipitating effect Effects 0.000 abstract 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- -1 ethylhexyl Chemical group 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- 125000005234 alkyl aluminium group Chemical group 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- GXWLHTAAGCHDAV-UHFFFAOYSA-L dichloro-bis(2-methylpropyl)stannane Chemical compound CC(C)C[Sn](Cl)(Cl)CC(C)C GXWLHTAAGCHDAV-UHFFFAOYSA-L 0.000 description 2
- YREAYUWMESCMHJ-UHFFFAOYSA-L didodecyltin(2+);dichloride Chemical compound CCCCCCCCCCCC[Sn](Cl)(Cl)CCCCCCCCCCCC YREAYUWMESCMHJ-UHFFFAOYSA-L 0.000 description 2
- SBOSGIJGEHWBKV-UHFFFAOYSA-L dioctyltin(2+);dichloride Chemical compound CCCCCCCC[Sn](Cl)(Cl)CCCCCCCC SBOSGIJGEHWBKV-UHFFFAOYSA-L 0.000 description 2
- INTLMJZQCBRQAT-UHFFFAOYSA-K trichloro(octyl)stannane Chemical compound CCCCCCCC[Sn](Cl)(Cl)Cl INTLMJZQCBRQAT-UHFFFAOYSA-K 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- 229940063656 aluminum chloride Drugs 0.000 description 1
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960004132 diethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- XBEXIHMRFRFRAM-UHFFFAOYSA-N tridodecylalumane Chemical compound CCCCCCCCCCCC[Al](CCCCCCCCCCCC)CCCCCCCCCCCC XBEXIHMRFRFRAM-UHFFFAOYSA-N 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2208—Compounds having tin linked only to carbon, hydrogen and/or halogen
Definitions
- the invention generally relates to organic tin compounds and is particularly directed to a method for the preparation of dialkyl-tin-dichlorides whose alkyl groups each contain 1 to 22 carbon atoms.
- Both methods have in common that in a first method stage, tetraalkyl-tin is first produced while, in a second method stage, alkyl-tin-chloride is prepared by comproportionation of the tetraalkyl-tin with tin-(IV)-chloride.
- dialkyl-tin-dichloride is produced by adding trialkyl-aluminum slowly to a solution of tin-diacetate-dichloride in tetrahydrofuran in a mole ratio of about 2:3.
- the aluminum-triacetate which precipitates during the course of the reaction is removed by filtration, while the tetrahydrofuran used as solvent is removed by distillation.
- the alkyl groups of the trialkyl-aluminum, used as starting material, are linear or branched and each has 1 to 22 carbon atoms. Linear alkyl groups are preferred. Trialkyl-aluminum compounds in which the three alkyl groups are the same are particularly preferred. Examples of suitable alkyl groups are methyl, ethyl, propyl, i-propyl, butyl, i-butyl, octyl, ethylhexyl, decyl, stearyl and behenyl.
- a preferred embodiment of the inventive method is characterized in that the reaction mixture, during the addition of the trialkyl-aluminum, has a temperature of about 5° to 60° C.
- the reaction mixture during the addition of the trialkyl-aluminum is maintained at a temperature of about 10° to 40° C. Since the reaction proceeds exothermally, the reaction mixture generally has to be cooled to maintain the indicated temperature range.
- Tetrahydrofuran is replaced by other solvents or liquid hydrocarbons such as, for example, diethylether, dibutylether, mono- and diglyme as well as toluene, the partial alkylation does not proceed in the same pronounced manner as with tetrahydrofuran and larger amounts of by-products are usually formed. Tetrahydrofuran is therefore the preferred solvent.
- inventive method has substantial advantages as compared to the state of the art as indicated above. Since it is a direct, one-step process, the preceding preparation of tetraalkyl-tin and subsequent comproportionation of tetraalkyl-tin with tin-(IV)-chloride are rendered unnecessary.
- dialkyl-tin-dichlorides obtained pursuant to the inventive method are suitable for improving glass surfaces and are also useful as intermediaries in the production of tin organic compounds.
- the aluminum-triacetate formed as by-product is a valuable catalyst in reesterification, esterification and polycondensation reactions.
- Aluminum-triacetate preciptates The acetate is removed by filtration through a sintered glass disc connectable to a vacuum source and is washed four times with about 100 ml tetrahydrofuran each time. The aluminum-triacetate so washed is dried in the filtering device under vacuum (1 to 3 mbar) at room temperature. 27.2 gram of aluminum-triacetate were obtained.
- the entire wash liquor is combined with the filtrate.
- the clear solution thus obtained is subjected in a water jet vacuum (about 18 mbar) to distill off the tetrahydrofuran.
- trioctyl-aluminum 5% excess were added to the solution under stirring and in dropwise manner. The addition time by drops was about 1 hours.
- Aluminum-triacetate precipitated which, through a filter disc connectable to a vacuum source, was removed by filtration and was subsequently washed 4 times with about 100 ml tetrahydrofuran each time.
- the washed aluminum-triacetate was dried in the filtering device under vacuum conditions (1 to 3 mbar) and at room temperature. 26.3 gram of aluminum-triacetate were obtained.
- the pre- or first running distillation amount comprises monooctyl-tin-trichloride and dioctyl-tin-trichloride in substantially equal amounts.
- the main distillation amount consists of dioctyl-tin-dichloride.
- the yield was 2.05 gram of monooctyl-tin-trichloride and 77.95 gram of dioctyl-tin-dichloride.
- the yield was 99.6 gram of didodecyl-tin-dichloride.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4007745 | 1990-03-12 | ||
| DE4007745A DE4007745C1 (de) | 1990-03-12 | 1990-03-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US5055603A true US5055603A (en) | 1991-10-08 |
Family
ID=6401957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US07/648,574 Expired - Fee Related US5055603A (en) | 1990-03-12 | 1991-01-31 | Method for the preparation of dialkyl-tin-dichlorides |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US5055603A (de) |
| EP (1) | EP0446703B1 (de) |
| DE (2) | DE4007745C1 (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090131704A1 (en) * | 2005-07-12 | 2009-05-21 | Arkema Vlissingen | Process for the Preparation of Monoalkyltin Trihalides and Dialkyltin Dihalides |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3036103A (en) * | 1959-05-21 | 1962-05-22 | Monsanto Chemicals | Preparation of trialkyltin halides and tetraalkyltin compounds |
| DE1157617B (de) * | 1959-04-30 | 1963-11-21 | E H Karl Ziegler Dr Dr | Verfahren zur Herstellung von einheitlichen Zinnalkylverbindungen |
| US3287386A (en) * | 1959-04-30 | 1966-11-22 | Ziegler Karl | Process for the production of tin alkyl compounds |
| EP0158163A1 (de) * | 1984-03-30 | 1985-10-16 | Schering Aktiengesellschaft | Herstellung von Organozinn-halogeniden durch katalysierte Redistribution von höher alkylierten Organozinn-Verbindungen mit niedriger alkylierten |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4322363A (en) * | 1980-07-28 | 1982-03-30 | Ppg Industries, Inc. | Method for making dibutyltin difluoride |
-
1990
- 1990-03-12 DE DE4007745A patent/DE4007745C1/de not_active Expired - Lifetime
-
1991
- 1991-01-31 US US07/648,574 patent/US5055603A/en not_active Expired - Fee Related
- 1991-02-27 EP EP91102862A patent/EP0446703B1/de not_active Expired - Lifetime
- 1991-02-27 DE DE59104280T patent/DE59104280D1/de not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1157617B (de) * | 1959-04-30 | 1963-11-21 | E H Karl Ziegler Dr Dr | Verfahren zur Herstellung von einheitlichen Zinnalkylverbindungen |
| US3287386A (en) * | 1959-04-30 | 1966-11-22 | Ziegler Karl | Process for the production of tin alkyl compounds |
| US3036103A (en) * | 1959-05-21 | 1962-05-22 | Monsanto Chemicals | Preparation of trialkyltin halides and tetraalkyltin compounds |
| EP0158163A1 (de) * | 1984-03-30 | 1985-10-16 | Schering Aktiengesellschaft | Herstellung von Organozinn-halogeniden durch katalysierte Redistribution von höher alkylierten Organozinn-Verbindungen mit niedriger alkylierten |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090131704A1 (en) * | 2005-07-12 | 2009-05-21 | Arkema Vlissingen | Process for the Preparation of Monoalkyltin Trihalides and Dialkyltin Dihalides |
| US7592472B2 (en) * | 2005-07-12 | 2009-09-22 | Arkema Vlissingen | Process for the preparation of monoalkyltin trihalides and dialkyltin dihalides |
Also Published As
| Publication number | Publication date |
|---|---|
| DE59104280D1 (de) | 1995-03-02 |
| EP0446703A2 (de) | 1991-09-18 |
| EP0446703B1 (de) | 1995-01-18 |
| EP0446703A3 (en) | 1992-08-19 |
| DE4007745C1 (de) | 1991-05-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: TH. GOLDSCHMIDT AG, GOLDSCHMIDTSTRABE 100, 4300 ES Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:RUF, ERICH;REEL/FRAME:005590/0437 Effective date: 19910114 |
|
| FPAY | Fee payment |
Year of fee payment: 4 |
|
| REMI | Maintenance fee reminder mailed | ||
| LAPS | Lapse for failure to pay maintenance fees | ||
| FP | Lapsed due to failure to pay maintenance fee |
Effective date: 19991008 |
|
| STCH | Information on status: patent discontinuation |
Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362 |